This invention relates to a novel class of arylsulfonylureidofuro[2,3-d]pyrimidines and their use as herbicides and plant growth regulants.
In U.S. Pat. No. 4,199,584, compounds of the following type are taught as pesticides: ##STR1##
U.S. Pat. No. 4,169,719, issued Oct. 2, 1979 to George Levitt, teaches arylsulfonylureidopyrimidines such as N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-chlorobenzenesulfonamide.
In U.S. Pat. No. 4,191,553, there is a disclosure of compounds having the formula: ##STR2## wherein R.sub.1 is H, OCH.sub.3 or alkyl of 1-3 carbons;
R.sub.2 is H, Cl, F, Br, NO.sub.2, alkyl of 1-4 carbons, alkoxy of 1-4 carbons, ##STR3## R.sub.3 is H, Cl, F, Br, CH.sub.3, or alkoxy of 1-4 carbons; R.sub.4 is H, Cl, F, Br, NO.sub.2, alkyl of 1-4 carbons, alkoxy of 1-4 carbons, ##STR4## R.sub.5 is H, Cl, F, Br, CH.sub.3, NO.sub.2 or CF.sub.3 ; R.sub.6 is H, Cl, F, Br, alkyl of 1-4 carbons or alkoxy of 1-4 carbons; PA1 R.sub.7 is Na+O--, OH, or alkoxy of 1-4 carbons; PA1 X is CH.sub.3, CH.sub.3 CH.sub.2, alkoxy of 1-3 carbons, CH.sub.3 OCH.sub.2, CH.sub.3 OCH.sub.2 CH.sub.2 O, CH.sub.3 S, CH.sub.3 CH.sub.2 S, CF.sub.3 or Cl; PA1 Y is CH.sub.3, CH.sub.3 CH.sub.2, alkoxy of 1-3 carbons, CH.sub.3 OCH.sub.2, CH.sub.3 OCH.sub.2 CH.sub.2 O, CH.sub.3 S or CH.sub.2 CH.sub.3 S; and PA1 Z is CH or N; PA1 only one of R.sub.2, R.sub.3 or R.sub.4 is alkoxy; and PA1 when R.sub.5 is NO.sub.2, R.sub.4 is other than NO.sub.2. PA1 Z is H or CH.sub.3 ; PA1 R.sup.1 is H, F, Cl, Br, CF.sub.3, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or NO.sub.2 ; PA1 R.sup.4 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.6 alkoxy, benzyloxy, C.sub.3 -C.sub.6 alkenyloxy, C.sub.3 -C.sub.6 alkynyloxy, C.sub.2 -C.sub.6 haloalkoxy substituted with 1-3 atoms selected from F, Cl or Br, C.sub.5 -C.sub.6 cycloalkoxy, O(CH.sub.2 CH.sub.2 O).sub.n R.sup.10, OCH.sub.2 CH.sub.2 CH.sub.2 OR.sup.10, OCH.sub.2 OR.sup.5, OCH.sub.2 OCH.sub.2 CH.sub.2 OR.sup.10, NR.sup.11 R.sup.12 or C.sub.1 -C.sub.4 alkylthio; PA1 m is 0, 1 or 2; PA1 n is 1 or 2; PA1 R.sup.5 is C.sub.1 -C.sub.4 alkyl; PA1 R.sup.6 and R.sup.7 are independently C.sub.1 -C.sub.4 alkyl, provided that the total number of carbon atoms of R.sup.6 and R.sup.7 is less than or equal to 5; PA1 B is O or S(O).sub.m ; PA1 R.sup.8 is CHF.sub.2, CF.sub.3, CH.sub.2 CF.sub.3 or CF.sub.2 CHFG where G is F, Cl, Br or CF.sub.3 ; PA1 R.sup.9 is C.sub.1 -C.sub.4 alkyl, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3, or C.sub.1 -C.sub.4 alkyl substituted with 1-3 atoms of F, Cl or Br; PA1 L is Cl, Br, C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.4 alkenyloxy, OH, S(O).sub.m R.sup.5, CO.sub.2 R.sup.17 or SO.sub.2 N(CH.sub.3).sub.2 ; PA1 R.sup.10 is CH.sub.3 or C.sub.2 H.sub.5 ; PA1 R.sup.11 is H, C.sub.1 -C.sub.4 alkyl, OCH.sub.3 or ##STR8## R.sup.12 is H or C.sub.1 -C.sub.4 alkyl; R.sup.11 and R.sup.12 can also be taken together to form --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; PA1 n' is 0 or 1; PA1 R.sup.13 is H, F, Cl, Br, NO.sub.2, CN, CF.sub.3, C.sub.1 -C.sub.3 alkyl, OCH.sub.3 or SCH.sub.3 ; PA1 R.sup.14 is H, F, Cl, Br, CH.sub.3 or OCH.sub.3 ; PA1 R.sup.2 is H, F, Cl, Br, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, NO.sub.2, CO.sub.2 R.sup.15, S(O).sub.m R.sup.16, SO.sub.2 NR.sup.18 R.sup.19 or SO.sub.2 N(OCH.sub.3)CH.sub.3 ; PA1 R.sup.15 is C.sub.1 -C.sub.4 alkyl; PA1 R.sup.16 is C.sub.1 -C.sub.3 alkyl; PA1 R.sup.17 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyloxy, CH.sub.2 CH.sub.2 OCH.sub.3 or CH.sub.2 CH.sub.2 Cl; PA1 R.sup.18 and R.sup.19 are independently CH.sub.3 or C.sub.2 H.sub.5 ; PA1 W' is O or S; PA1 R.sup.3 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, H, F, Cl, Br, NO.sub.2, SO.sub.2 MR.sup.6 R.sup.7, SO.sub.2 N(OCH.sub.3)CH.sub.3 or C(O)R.sup.4 ; PA1 R.sup.20 is F, Cl, Br, CO.sub.2 R.sup.17, OSO.sub.2 R.sup.9, No.sub.2, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; PA1 W is O or S; PA1 X is CH.sub.3, C.sub.2 H.sub.5, Cl, OCH.sub.3, OC.sub.2 H.sub.5, N(CH.sub.3).sub.2 or SCH.sub.3 ; PA1 Y is H, CH.sub.3 or C.sub.2 H.sub.5 ; PA1 (a) when R.sup.11 is OCH.sub.3 ; then R.sup.12 is CH.sub.3 ; PA1 (b) if R.sup.1 is other than H and R is H, then R.sup.1 cannot be in the 4-position of the benzene ring; PA1 (c) when R.sup.11 is ##STR9## then R.sup.12 is H or CH.sub.3 ; and (d) when W' is O, then R.sup.3 is CO.sub.2 R.sup.17. PA1 W is O; PA1 Y is CH.sub.3 ; PA1 X is other than Cl; PA1 A is other than ##STR10## and Z is H; PA1 X is CH.sub.3 or OCH.sub.3 ; and PA1 A is ##STR11## PA1 X is CH.sub.3 or OCH.sub.3 ; and PA1 A is ##STR12## PA1 X is CH.sub.3 or OCH.sub.3 ; and PA1 A is ##STR13## PA1 R is C.sub.1 -C.sub.3 alkyl, OCH.sub.3, F, Cl, Br, NO.sub.2, CF.sub.3, C(O)R.sup.4, S(O).sub.m R.sup.5, SO.sub.2 NR.sup.6 R.sup.7, SO.sub.2 N(OCH.sub.3)CH.sub.3, BR.sup.8, OSO.sub.2 R.sup.9 or CH.sub.2 L; PA1 R.sup.4 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.4 alkenyloxy, haloethoxy containing 1-3 atoms of F or Cl, OCH.sub.2 CH.sub.2 OR.sup.10, OCH.sub.2 CH.sub.2 CH.sub.2 OR.sup.10, OCH.sub.2 OR.sup.5, OCH.sub.2 OCH.sub.2 CH.sub.2 OR.sup.10, NR.sup.11 R.sup.12 or C.sub.1 -C.sub.4 alkylthio; PA1 B is O; PA1 L is OCH.sub.3 or CO.sub.2 R.sup.17 ; PA1 R.sup.11 is C.sub.1 -C.sub.4 alkyl or OCH.sub.3 ; PA1 R.sup.12 is C.sub.1 -C.sub.4 alkyl; and PA1 R.sup.11 and R.sup.12 can be taken together to form --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --, PA1 R.sup.1 is H; PA1 R.sup.4 is C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.4 alkenyloxy, OCH.sub.2 CH.sub.2 Cl or OCH.sub.2 CH.sub.2 OCH.sub.3 ; PA1 R.sup.8 is CF.sub.3, CH.sub.2 CF.sub.3 or CF.sub.2 CHF.sub.2 ; PA1 R.sup.9 is CH.sub.3 ; and PA1 L is OCH.sub.3 ; PA1 R is NO.sub.2, C(O)R.sup.4, SO.sub.2 R.sup.5 or SO.sub.2 N(CH.sub.3).sub.2 ; PA1 R.sup.4 is C.sub.1 -C.sub.3 alkoxy; and PA1 R.sup.5 is C.sub.1 -C.sub.3 alkyl; PA1 A is ##STR14## and R.sup.2 is Cl, Br, CH.sub.3, OCH.sub.3 or S(O).sub.m CH.sub.3 ; PA1 W' is S; PA1 R.sup.3 is H, CH.sub.3, Cl, Br or C(O)R.sup.4 ; and PA1 R.sup.4 is C.sub.1 -C.sub.3 alkoxy. PA1 2-Chloro-N-[(4,6-dimethylfuro[2,3-d]pyrimidin-2-yl-aminocarbonyl]benzenesul fonamide, m.p. 200.degree.-201.degree. (d); PA1 N-[(4,6-Dimethylfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]-2-nitrobenzenesulf onamide, m.p. 204.degree.-205.degree. (d); PA1 2-[(4,6-Dimethylfuro[2.3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl benzoic acid, methyl ester, m.p. 197.degree.-198.degree. (d); PA1 2-[(4,6-Dimethylfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl benzoic acid, (2-propenyl)ester, m.p. 185.degree.-186.degree. (d); PA1 2-[(4,6-Dimethylfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl benzoic acid, (1-methylethyl)ester, m.p. 196.degree.-197.degree. (d); PA1 2-Chloro-N-[(4,6-dimethylfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]-3-pyridin esulfonamide, m.p. 206.degree.-207.degree. (d); PA1 3-[(4,6-Dimethylfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl-2-thi ophenecarboxylate, methyl ester, m.p. 202.degree.-203.degree. (d); PA1 N-[(4,6-Dimethylfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]-3-methyl-2-thiophe nesulfonamide; PA1 4-[(4,6-Dimethylfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl-3-thi ophenecarboxylate, methyl ester; PA1 2-[[(4,6-Dimethylfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benz oic acid, ethyl ester, m.p. 193.degree.-195.degree. (d); PA1 2-[[(4-Methoxy-6-methylfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfony l]benzoic acid, methyl ester, m.p. 216.degree.-218.degree.; PA1 N-[(4,6-Dimethylfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]-2-methylsulfonylbe nzenesulfonamide, m.p. 208.degree.-210.degree. (d); and PA1 N'-[(4,6-Dimethylfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]-N,N-dimethyl-benz ene-1,2-sulfonamide, m.p. 199.degree.-202.degree.. PA1 M is H or an alkali metal; PA1 W' is O or S; PA1 W is O or S; PA1 X is CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3 or OC.sub.2 H.sub.5 ; and PA1 Y is H, CH.sub.3 or C.sub.2 H.sub.5. PA1 where R is NH.sub.2, CN, S(O)R.sup.5, CH.sub.2 OH, CH.sub.2 S(O)R.sup.5, CH(CH.sub.3)OH, CH(CH.sub.3)S(O)R.sup.5 ; or PA1 where R.sup.2 is S(O)R.sup.16 ; or PA1 where R.sup.4 is H, C.sub.1 -C.sub.3 alkyl, OCH.sub.2 OR.sup.5, C.sub.3 -C.sub.6 alkynyloxy, OCH.sub.2 OCH.sub.2 CH.sub.2 OR.sup.10, NR.sup.11 R.sup.12 or C.sub.1 -C.sub.4 alkylthio.
provided that
Unexamined European Pat. No. 7687, teaches arylsulfonylureidopyrimidines such as N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulf onamide.
In the Bull. Soc. Chim. Fr., 803 (1969), the authors, Bisagni etc. teach the compound 2-amino-4,6-dimethylfuro[2,3-d]pyrimidine.
In Chem. Ber., 106, 874 (1973), Wolfers et al. teach 2-amino-6-phenylfuro[2,3-d]pyrimidines.
In addition, 4-aminofuro[2,3-d]pyrimidines are well known in the art, see for example, Japan. Kokai 73 78,199 [Chem. Abstr. 80 96012f (1974)] wherein the following is taught: ##STR5##
In Chem. Ber., 99 (3), 1002 (1966), the following compound is taught: ##STR6##
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food needs, such as rice, corn, wheat, soybean and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing the loss of a portion of such valuable crops by killing or inhibiting the growth of undesired crops is one way of improving this efficiency.
A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need exists, however, for still more effective herbicides that destroy or control weeds without causing significant damage to useful crops.